Water → HCID 10208855, compound

HRID 1835355Notes

Reaction equation

HRID 1835355 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([C:13]([CH3:43])([CH3:42])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([C:31]#[C:32][CH2:33][O:34][Si](C(C)(C)C)(C)C)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]([CH3:42])([CH3:43])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([C:31]#[C:32][CH2:33][OH:34])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH3:17])=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:44])[F:45])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 23502793HCID 23502793, compound

Product 1

HCID 10208855HCID 10208855, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 167 mg (0.257 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-{6-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-4-o-tolyl-pyridin-3-yl}-N-methyl-isobutyramide in 1.5 ml tetrahydrofuran a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran was added at room temperature. After stirring for 0.5 h water was added, followed by extraction with four portions of ethyl acetate. The combined organic extracts were dried with sodium sulfate and concentrated. Column chromatography afforded 82 mg (60%) of the title compound as a brown viscous oil.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with four portions of ethyl acetate
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-560c5039cd9840f68b6fc3195dee8cec
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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